Q5: give chat wakes timed, attributed history apart from the new ask

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

tests/integration/ceo-founder-chat.test.ts

@@ -121,7 +121,7 @@ describe("founder⇄CEO chat", () => {
 
     // The CEO's prompt names the human principal, not just another teammate.
     expect(capturedWakePrompts).toHaveLength(1);
-    expect(capturedWakePrompts[0]).toContain("[Yang (founder)]: How are we tracking against the MVP?");
+    expect(capturedWakePrompts[0]).toMatch(/\] Yang \(employee, Board Chair\): How are we tracking against the MVP\?/);
 
     // The reply landed in the SAME pinned conversation and thread — to="Yang"
     // resolves the employee and ensureDirectSpace reuses the founder's line.

tests/integration/chat-context.test.ts

@@ -0,0 +1,102 @@
+import { randomUUID } from "node:crypto";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { describe, expect, test } from "vitest";
+import { DatabaseConnection } from "../../src/main/database/connection";
+import { OnboardingService } from "../../src/main/services/onboarding-service";
+import { ProviderService } from "../../src/main/services/provider-service";
+import { providerAdapters } from "../../src/main/services/provider-adapters";
+import { TaskExecutionService } from "../../src/main/services/task-execution-service";
+import { ChatService } from "../../src/main/services/chat-service";
+import { ensureCeoDirectSpace } from "../../src/main/services/ceo-direct-space";
+import { claimNextQueuedRun } from "../../src/main/app/task-queue-worker";
+import type { AgentTurnResult, ProviderToolTurnInput } from "../../src/main/services/provider-tool-turn";
+
+const testVault = {
+  encryptSecret: (secret: string) => Buffer.from(secret, "utf8"),
+  decryptSecret: (ciphertext: Buffer) => ciphertext.toString("utf8"),
+};
+
+async function founderLine() {
+  const wakePrompts: string[] = [];
+  const turn = async (input: ProviderToolTurnInput): Promise<AgentTurnResult> => {
+    const first = input.messages.find((message) => message.role === "user");
+    const prompt = first && first.role === "user" ? first.text : "";
+    if (/thread_id="/.test(prompt) && input.messages.length === 1) wakePrompts.push(prompt);
+    return { text: `Reply ${wakePrompts.length}.`, toolCalls: [], rawResponseJson: "{}" };
+  };
+  const connection = new DatabaseConnection(join(tmpdir(), `ac-chatctx-${randomUUID()}.db`));
+  const providers = new ProviderService(connection.db, providerAdapters, testVault, undefined, turn);
+  const onboarding = new OnboardingService({ db: connection.db, saveProviderCredential: (input) => providers.saveCredential(input) });
+  const execution = new TaskExecutionService(connection.db, providers);
+  const chat = new ChatService(connection.db);
+  let orgId = "";
+  let ceoId = "";
+  connection.transaction(() => {
+    const summary = onboarding.bootstrap({
+      companyName: "FlowPilot", companyDescription: "CSM analytics.", employeeName: "Yang", workspacePath: "",
+      executionMode: "ai_ceo", autoApproveHires: true, reviewDeliverables: false,
+      goalTitle: "Ship the MVP.", goalDescription: "A working product.",
+      providerKey: "openai", providerSecret: "sk-test-key", providerModel: "gpt-5.4",
+    });
+    orgId = summary.orgId;
+    ceoId = summary.ceoAgentId;
+  });
+  const founderId = (connection.db.prepare("select id from employees where org_id = ?").get(orgId) as { id: string }).id;
+  const spaceId = ensureCeoDirectSpace(connection.db, orgId)!;
+  const kickoff = claimNextQueuedRun(connection);
+  await execution.executeRun(kickoff!.org_id, kickoff!.id);
+  const say = (bodyMd: string, threadId: string | null) => {
+    const id = chat.sendMessage({ orgId, spaceId, threadId, senderType: "employee", senderId: founderId, bodyMd, attachmentFileIds: [] });
+    return (connection.db.prepare("select thread_id from chat_messages where id = ?").get(id) as { thread_id: string }).thread_id;
+  };
+  const runWake = async () => {
+    const wake = connection.db.prepare(
+      "select id from task_runs where org_id = ? and agent_id = ? and trigger = 'chat_mention' and state = 'queued'",
+    ).get(orgId, ceoId) as { id: string };
+    await execution.executeRun(orgId, wake.id);
+  };
+  const edit = (bodyMd: string, newBody: string) => {
+    const row = connection.db.prepare("select id from chat_messages where body_md = ?").get(bodyMd) as { id: string };
+    chat.editMessage({ orgId, messageId: row.id, bodyMd: newBody, actorType: "employee", actorId: founderId });
+  };
+  return { connection, wakePrompts, say, runWake, edit };
+}
+
+describe("chat wake context", () => {
+  test("separates what the agent already answered from what is new, with times and senders", async () => {
+    const h = await founderLine();
+    const threadId = h.say("How are we tracking?", null);
+    await h.runWake();
+    h.say("Also, who owns billing?", threadId);
+    h.say("And ship date?", threadId);
+    await h.runWake();
+
+    const prompt = h.wakePrompts[1];
+    const earlier = prompt.slice(prompt.indexOf("Earlier in this thread"), prompt.indexOf("New since your last reply"));
+    const fresh = prompt.slice(prompt.indexOf("New since your last reply"));
+    expect(earlier).toContain("How are we tracking?");
+    expect(earlier).toContain("Reply 1.");
+    expect(fresh).toContain("Also, who owns billing?");
+    expect(fresh).toContain("And ship date?");
+    expect(fresh).not.toContain("How are we tracking?");
+    expect(fresh).toMatch(/\[\d{4}-\d{2}-\d{2} \d{2}:\d{2} UTC\] Yang \(employee, Board Chair\)/);
+    expect(earlier).toMatch(/\] CEO \(agent, [^)]+\): Reply 1\./);
+    h.connection.close();
+  });
+
+  test("a message corrected after the agent's reply counts as new", async () => {
+    const h = await founderLine();
+    const threadId = h.say("Ship on Monday.", null);
+    await h.runWake();
+    h.edit("Ship on Monday.", "Ship on Friday.");
+    h.say("See the correction above.", threadId);
+    await h.runWake();
+
+    const prompt = h.wakePrompts[1];
+    const fresh = prompt.slice(prompt.indexOf("New since your last reply"));
+    expect(fresh).toMatch(/Yang \(employee, Board Chair\) \(edited \d{4}-\d{2}-\d{2} \d{2}:\d{2} UTC\): Ship on Friday\./);
+    expect(fresh).not.toContain("Reply 1.");
+    h.connection.close();
+  });
+});